Nickel Phosphite-Catalyzed Tetradehydro-Diels-Alder Reactions of (E)-3-ene-1,8-diynes

Liam M Joyce; Stephen A Moggach; Christopher J T Hyland; Stephen G Pyne; Scott G Stewart

doi:10.1021/acs.joc.2c03040

Nickel Phosphite-Catalyzed Tetradehydro-Diels-Alder Reactions of (E)-3-ene-1,8-diynes

J Org Chem. 2023 May 5;88(9):5391-5402. doi: 10.1021/acs.joc.2c03040. Epub 2023 Apr 10.

Authors

Liam M Joyce^{1

2}, Stephen A Moggach¹, Christopher J T Hyland³, Stephen G Pyne², Scott G Stewart¹

Affiliations

¹ School of Molecular Sciences, The University of Western Australia (M310), 35 Stirling Highway, Crawley, WA 6009, Australia.
² School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales 2522, Australia.
³ Molecular Horizons Research Institute, School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales 2522, Australia.

PMID: 37036249
DOI: 10.1021/acs.joc.2c03040

Abstract

A nickel-catalyzed tetradehydro-Diels-Alder reaction of (E)-3-ene-1,8-diynes for the preparation of isoindolines, dihydroisobenzofurans, and tetrahydroisoquinolines has been developed. A series of air-stable nickel catalysts were used in this study, including the novel nickel(0)-phosphite catalysts, Ni[P(O-3,5-Me-Ph)₃]₄, Ni[P(O-1-naphthyl)₃]₄, and Ni[P(O-2-naphthyl)₃]₄. To help understand the type of intermediate in the initial cycloisomerization process, the trapping of nickellacycle intermediates with pinacolborane to yield vinyl boronates is also discussed.